


Auto-Pilot

by madelinewrites



Category: Supernatural
Genre: Angst, Existential Crisis, F/M, Fluff, Fluffy Angst, flangst, fluff/angst, lovey, romantic
Language: English
Status: Completed
Published: 2016-08-05
Updated: 2016-08-05
Packaged: 2018-07-29 11:02:55
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,176
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7681915
Author URL: https://archiveofourown.org/users/madelinewrites/pseuds/madelinewrites
Summary: <blockquote class="userstuff">
              <p>AU: Where reader and Dean are both children of very successful, but opposing, businesses and are being pushed together to combine the companies profits and success. As much as Dean loves his soon-to-be-wife, he can’t help feeling guilty, forcing Y/N into loving him back, even if it is under their parent’s controlling hands.</p>
            </blockquote>





	Auto-Pilot

**Author's Note:**

> Phew, this took awhile. It turned out much longer than expected, just had a lot to say I guess. It’s mostly very sweet and lovey, with a moment of existential crisis (gotta express it somewhere). Hope you enjoy! As always, I LOVE FEEDBACK!!

** **

**“You don’t have to say I love you to say I love you. Forget all the shooting stars and all the silver moons. We’ve been making shades of purple out of red and blue. Sickeningly sweet like honey, don’t need money. All I need is you” — Troye Sivan, _for him._**

Slowly, I began buttoning up my tweed cardigan, my eyes glazed over as I tried to focus on the task. I stared at myself in the mirror for a moment once I was done, feeling a tear fall down my face. It was unlike me, but it just seemed like too much. I slowly looked to the little, expensive, black box on my nightstand, a simple reminder of what I was being forced to do.

             I loved Y/N. That was never the problem. Undeniably beautiful, can be cute or sexy, can make you laugh so hard you can’t breathe or want to scream until your lungs are raw. She was classy and sloppy, she was good and evil, she was hot and cold. She everything for any mood rapped up into this one ethereal human, and I loved her with every twist and turn that she was made of. So my love for her was never arranged, never forced. It was her lack of love for me that created the complications.  

             I knew I was a little rough around the edges; I could be moody and bitter, and god-forbid I revealed emotion. She made me feel like I was different though, made me want to be a different, better Dean. Maybe she didn’t see any potential in me, and I couldn’t blame her because I didn’t either. And yet she, with all her amazing qualities, was going to be forced to be with me.

             Sam was actually the face of our business, the one everyone would see in our company speeches and advertisements. Dad may have been the CEO, but Sam was who everyone thought of when they heard _Winchester In-corporations._ Dad always made sure to remind me of this, how we had to do it for Sammy. My dad had said when first telling me of the arrangement, that marriage didn’t always mean happiness. If it was for the best of the company and for our pockets, then it was the right thing, no matter the cost. At least, that was the way his mind worked. I think it was because of mom and the fire; I don’t think dad looked at things the same after she died and he somehow managed to pass on his bitter attitude to me. No matter how much like him I could be, and how much like him I wanted to be, I just couldn’t seem to understand him with the arranged marriage. Business success or no, shouldn’t my happiness be of a higher priority than a line on a graph going up at the end?

             Our businesses had been longtime adversaries; both our products good, but missing something the other company had. There was no denying that coming together was a great business plan, I had even gotten the idea in dad’s head to begin with. I never imagined he would lay out something as binding as marriage or that he would sacrifice me in the process. I had argued with him for hours, telling him all these points, rebutting all his arguments as he had taught me to do in a debate. Yet, the argument still ended with that knowing look of his, and the words he said hadn’t stopped repeating in my head since they left his mouth.

             “Say what you will and battle it as much you want son, but you’ve been waiting for this opportunity since you saw her at the pool in sixth grade. You’re not fighting this for you.”

             It just continued on in my head like some sort of strange, condescending mantra. I just couldn’t seem to drop it, and that was because it was true. I was doing it for her because, damn, did I want her as mine, but never without her wanting me as hers as well. Never like that. Still, there was a strange thrill in me at the thought of what was to come, of getting down on one knee and pulling out that ring that I had spent hours upon hours deciding upon. To her that moment would be the casting of a curse she would be forced to live with forever.

             My phone began to buzz as I moped about the whole damned situation and how wrong it all was, my soon-to-be-wife the caller.

             “Hey Dean,” Y/N greeted, her voice shaking slightly. “You said six right?”

             “Yeah, Y/N, six. Why, is that still okay?” I replied, a little too eager to please.

             “Uh, well…no, I guess not,” she sighed, stress evident in her tone.

             “What’s wrong? Do you need help?” I began grabbing my things, stuffing the little box into my pocket, already headed out the door.

             “Maybe, uh, maybe we should just cancel tonight huh? I’m not near ready and everything is just a colossal mess right now and…”

             “Y/N, Y/N, Y/N,” I interrupted. “Stop for a second. _Breathe_. Jesus, you’re like that chick from _The Devil Wears Prada_.”

             “You’ve seen that?”

             “Um…” I mumbled.

             “Whatever. Just give me till like…8:30, okay?” Y/N cut in.

             “What’s going on?”

             “It’s really nothing, Dean. I’ll see you at 8:30.” The beeping of a call’s end sounded, leaving me frustrated and worried. I continued down to my personal car garage, picking my favorite even among the newer and faster vehicles; my baby, the ’67 Impala. Y/N was one of the few outside of my family to see baby in action; I never dared bring it to the “fun”, required upper class parties I was forced to attend. Y/N never failed to compliment the classic vibe, fond of the change of pace from all the monotonous 60,000$ cars we were surrounded by. The thought just made my feet move quicker, the distance between us seem longer.

             I arrived at Y/N’s about an hour later, the drive to her private cottage always a killer, slightly sweaty even with the A/C on full blast. I remember years ago, at one of those parties I hated, she was divulging the tale of convincing her father that she didn’t _want_ the huge mansion in the heart of California; she wanted privacy, something small that wouldn’t require much cleanup. Of course she had won, her wit and charm something I could never fathom. I sat for a moment outside her house, drumming my fingers on the wheel, my thoughts flooding in as a cruel reality check. Y/N rarely did things like this, even if she was late she wouldn’t _admit_ to it. It could’ve been an excuse to get out the date, maybe she got wind of the events planned for the night and was already boarding a plane to China. As much as my instincts screeched to every atom of my being to run away like the coward I was, I also couldn’t stop imagining her hurt in some way. The thought stopped my procrastination, and I headed up to her porch.

             I knocked gently, then more forcefully when she didn’t respond.

             “Y/N! It’s Dean, you know,” I called. “Of Winchester Incorporation?”

             I could hear the relieved sigh from her and then the snicker of condescension.

             “I know your stupid business Dean,” Y/N laughed, opening up the door. “You know, company enemy thing and all?”

             I would have continued to make light of my brainwashed mind, but my thoughts were consumed by the sight of her usually-quaint-yet-beautiful cottage. Her art pieces, something that she found an abundant amount of joy in, were away from their usual homes of cases and frames on walls, but were strewn in pieces all over the floor. Her couch had rips in it; the wood floor was scraped to hell. It was as though a werewolf had a tantrum and took it out on her. 

             “Dear _God_ , Y/N,” I gasped, worry and shock creating a tremor in my voice. “What the hell happened? Are you alright?” I looked her over, grabbing her arms gently and taking her in. She didn’t seem physically hurt, but stress was evident in her features, a gloss over her eyes. She clenched her jaw, blinking away the gloss, a futile effort to hide her misery. She reminded me of myself.

             “Yes, yes, I’m alright. It’s my house that’s suffering.” My eyes wouldn’t quit shooting all over her body, checking for any possible scrapes or bruises.

             “Who, or _what_ , did this?” I asked, finally looking back to her eyes. She shuffled her feet slightly, her hand going up to twiddle with her hair nervously.

             “Well,” she began, embarrassment marring her tone. “I guess the fact that it won’t impress guests isn’t the only downfall to this house. I thought I wasn’t famous enough for people to try and figure out where I live. Guess I was wrong. I guess you’re not the only business that hates us.”

             I stood for a moment not believing what I was being told. “Y/N, you’re the child of one of the biggest businesses in the world, and you don’t even have an alarm system, let alone some kind of guard?”

             Her eyes became determined, her jaw jutting out in defiance. “I didn’t want an alarm system. I didn’t want guards. I haven’t lived in a place that feels like home since my dad took over the business, I just wanted to have one place where I could just feel like my life was normal, like I had some say in what my life consists of. I guess that dream has to be dashed now, though.”

             I wanted to keep on the topic, to get some reason in her, but yet a part of me related too much to defy her. My dad had brought me into this life as a support system for my brother’s business, as a pretty face to try and charm our way into good deals. The life of a business family didn’t just consume all friendships or outer-world views of you, it managed to infiltrate your family too. Being alone seemed to be the only way to get away from it, and that time wasn’t filled with comfort and bliss; it was always this strange feeling of pure deadness, like a flower left to rot. I couldn’t yell at her for making a naive move, because most other people don’t have to get alarm systems if they don’t want to, and most people are allowed to feel comfortable without having to hide away from the entire world. Money and fame could be a high, but the crash of the drug came too soon, and one did whatever they could once the high stopped feeling good.

             “Tell you what,” I quipped. “I’ll clean up- or, begin to, at least- and you go get ready. You obviously don’t need to, but I want you to feel good, I want us to have a good time, among all the shit.” _Just as I want our lives to be_.

             “I don’t know Dean, I can’t make you clean this up,” Y/N wavered, messing with her hair once more.

             “You’re not going to be able to let it go until it’s better, so let me make it better, honey.” I stiffened immediately at the endearment that fell out of my mouth, I mean _Christ_ , we weren’t married yet. As much as I was infatuated by her, she could’ve truly hated me. She just smiled tenderly, though, her eyes softening at the warmness of my words.

             “Alright. Thank you so much for this, Dean.” She bounced quickly onto her tip-toes, pecking me on my cheek, having to hold my shoulders to keep balanced, before running off to her little bathroom. I entered into the door when she left my sight, closing and locking it behind me. I looked among the mess and blew out my breath, rolling up my sleeves as I warmed up for the work ahead of me.

             I sat on her couch, exhausted, a cold beer from her fridge in hand. I had cleaned up as much as I could, even trying to scrub some of the scratches from the floor. Some things would just have to be replaced; the couch cushion, broken art, torn curtains were all irrevocably damaged. Considering the turmoil that it began in, I did one hell of a job though.

             My spirits were quickly lifted to the heavens when she finally walked through the archway, her big eyes taking in the contrast of the living room alone. I set my drink on the coffee table, fixing my sleeves and my hair anxiously, my eyes never leaving her. Her hair fell in large, soft waves, tossed over one shoulder. Her dress fit her snugly in all the right places, sparkly and eye-catching, as if she didn’t already have my constant attention.

             “Dean, my gosh, how did you do it all so quick? It looks so much better than I ever thought it would again.” I smiled at her appreciation, too busy appreciating _her_ to really listen. I walked up to her slowly, our eyes connecting in a hot smolder. I grabbed her hand and kissed the top.

             “My pleasure,” I grumbled, my voice deeper than even I expected. Pink suddenly spread over her cheeks, her mouth forming into a sly smirk as she looked up at me through her lashes. “You look stunning.”

             “Well, thank you. We should probably get going before everything closes,” she whispered, her voice a little shaky. It was my turn to smirk.

             “Ah, don’t you worry about that. We have all night.” She grinned at my mischievous laugh, looping her arm into mine.

             “Well lead the way sir, might as well get the night started.”  

             Ever-so-politely I led her outside, helping her down the stairs of the porch. She snickered at the sight of my car.

             “Gotta love Baby, huh?”

             “Hell yeah, she’s such a beaut’,” I teased.

             “How long have you had her?” she asked as I opened the car door for her.

             “Since birth. She was my father’s, but he just started to leave it in his garage to rust, so I decided I was the only that would give her what she deserves.” Y/N laughed at my speech, but in a sincere, sad way. She understood.

             “Well,” she began once I got in the driver’s seat. “I’m honored to be riding in her. I know you only take her out every so often.”

“Hey, I’m just glad to finally have found someone who values her like I do.” I smiled sadly, reminiscing. “My mom used to do that for my dad. I couldn’t believe it when I had found Baby sitting with a layer of dust on her in dad’s garage; if mom was still around she’d kick his ass.”

             She laughed once more, a bit softer this time, but with the same underlying sympathy.  She kicked off her heels, curling her feet underneath her as we began the long drive towards our destination. It was a gorgeous area, I could understand wanting to hide out amongst all the lush trees and bushes. She had the guts to stand up to her father and get what she wanted. I respected the man to hell and back, but sometimes I just wanted my life to be mine and not my dad’s.

             “So,” she opened, thankfully breaking the road my thoughts were going down. “Are you and Samuel close?”

             I was confused for a moment, so comfortable with her that it seemed strange for her to be calling him by his business-esque full name.

             “Yeah. Probably a little too close for it to be healthy. I’ve always been protective, he’s my little brother you know, I gotta make sure he’s alright. My mom would’ve wanted that.”

             “And you too,” she interjected gently.

             “What?”

             “She would’ve wanted you to be alright too, Dean…  _Are_ you alright?” My jaw clenched, fingers tightening slightly around the driver’s wheel as the words left her mouth. I couldn’t answer for a moment because she was right; mom would’ve wanted me alright. She would’ve wanted me more than alright, she would want me happy and fulfilled and comfortable. That was clear to me. I just couldn’t figure out if _I was_ alright.

             “Yeah,” I lied nonchalantly. “You know, stressed from work constantly, but I’m fine.”

             “Hmm,” she replied. I turned on the radio, my music filling the car. She quickly turned it off.

             “Yeah, **_how about no?_** As much as I love that song, I want you to talk to me.”

             I swallowed. “I don’t know, Y/N. I don’t know what I am. Damn, I hardly know who I am.”

             She nodded. “I don’t either. Things will feel so good for some moments, and I’ll be real content and happy, and then it’s gone and it’s like I go on auto-pilot again. Just surviving, losing the idea of what living feels like.”

             “Depressing.”

             “But true.”

             “Yeah,” I agreed. “But true.”

             We were both silent then, minutes passing without a sound. It wasn’t awkward, just heavy.

             “What do you think you need? To make you happy, I mean? To make you feel alive?”

             She looked over at me, voice urgent even with the vague thought that she spoke. “I’ve had glimpses of it, lately. I just don’t know if how I picture it is how it really is.”

             “I guess it’s a matter of just going at what you want, whether it’s what anyone else wants or not. At least, that’s what I’m thinking,” I said, thinking out loud.

             “I always feel like I do that, but I wonder if I’m asking for what I really want or-“

             “Or if you’re just getting further from what you really want?”

             She breathed out, her face sad as I glanced over at her. “Yeah. Yeah, that pretty much sums it up.”

             The silence became suffocating, but neither of us wanted to say much more. So, this time, she was the one to turn on the radio. I didn’t turn it off.

             “Uhm,” Y/N said uncertainly. “Isn’t this just your house?”

             I chuckled. “Just you wait.”

              Y/N nodded, smiling that soft smile once more. I wondered how someone so beautiful, inside and out, could be contained into one being. I wondered if I would ever get over it. I wouldn’t.

             I parked in my garage, leading her past all my cars into the elevator. Instead of my normal button of floor 6, I sent us to the very top of my skyscraper apartment, a move in which she squealed at.  
             “We’re going to the top?”

             I just laughed, but she continued.  
             “Is that… safe? I mean heights aren’t my worst fear, but I really don’t want to, you know, _die_.” I couldn’t help but keep laughing at her, her face filled with an undeniable, shameless worry.

             “Y/N, trust me.” She quiets at this, looking at me seriously and nodding. It seemed with those simple words some sort of pact was made, and I felt proud that I would be able to hold it up.

             Even with as expensive as the apartment was, the elevator still took forever. I couldn’t help but glance at her a few times, sometimes to find her eyes glancing at me. Suddenly the ring felt like it was a hundred pounds in my pocket, and my stomach knotted with anticipation. Finally, the elevator dinged as we reached the roof, and I made sure to turn quick enough to get her reaction. I was very glad I did.

              Y/N gasped, her hand going to her mouth in pure shock, eyes wide as a child’s with disbelief. I grabbed onto one of her hands, leading her out for a better look. I planned for a whole garden of flowers to be arranged around the roof, at least fifty candles as the only lighting other than the city’s twinkling. Flowers from the elevator led to a picturesque little table, red wine ready and waiting to be poured and food ready to be eaten. The city’s buzz sounded soft from the roof, a distant buzz of life. I was even awed, even though I had been there to set it up earlier. At night, the setting was more than romantic.

             “Dean,” Y/N breathed, turning to face me. “I can’t believe…this is…Dean.” Her sentences were anything but coherent but I just nodded, smiling.

             “That,” I emphasized, pointing to her mouth. “Is what I was going for.” Suddenly her arms were around my neck, hugging my tightly.

             “Thank you for this,” she whispered into my ear before resting her head on my neck. We stood like that for a moment, taking in the feeling of each other.

             She pulled away and I rested my forehead on hers. “Let’s eat.”

             She laughed, grabbing my hand and pulling me towards the table. I pulled out her chair, even placing her napkin on her lap. She rolled her eyes at me, but it just felt appropriate. I just wanted to treat her how she deserved, if she was going to be stuck with me, she might as well be stuck with the best me possible.

             So we ate and we talked, drinking and laughing and gazing at the skyline dreamily. It seemed like hours that we sat, slap-happy and a little tipsy. Soon appetizers were gone, and then dinner, and then we were giggling over dessert, and then that was gone too. When we were finished, every scrap of food and every drop of wine was consumed. The time was then, and I knew I had to do it while things were perfect. I grabbed her hand and she stopped looking sadly at the empty wine to follow my guidance. I led her to the other side of the roof, the one hidden by where the elevator exit sat. The buildings went on seemingly forever, the bright lights never going out even with the time of night. I faced her, watching as she took it all in. As much as she was a city girl, she never seemed to tire of it. Her eyes were so shiny. I wondered if she could see the speed my blood was pumping through my veins. Without thinking, I was on one knee.  We were both shocked by the action, but I quickly recovered.

             “Y/N YM/N YL/N,” I expressed. “I know we live in such a crazy world with facades and staged love and staged happiness. And I know that I never would have had the balls to do this without my dad telling me I had to, but for once I’m thankful about being forced into something, because this is it Y/N. You’re what I want, what I actually truly want, and I want to be what makes you turn off that auto-pilot. So,” I pulled out the little box. “Y/N, would you do me the honor of being my wife? Will you marry me?”

              Y/N’s eyes were filled with tears, her hand outstretched to me.

             “Yes, Dean. Dear god, _yes_ ,” she exclaimed, giggling slightly. I just stared at her for a moment, completely shocked at the reception. I slid the ring on her finger quickly, as though if I didn’t do it in time she would leave. She pulled me from my knee and kissed me, slowly and passionately. I felt as though I could kiss her forever, just trying to savor and remember the feeling for when I wouldn’t have it. She pulled away after a while to breath, resting her forehead on mine.

             “I can’t tell you how long I’ve wanted this,” she murmured.

             “Really?” I couldn’t even fathom the idea.

             “My god, I think I’ve wanted you since sixth grade,” she stressed. I laughed, full of heart and happiness. I couldn’t believe I had even made it on her radar.

             “I love you, Y/N,” I testified simply, sincerely.

             “I love you too, Dean.”

             For a while we stayed like that, kissing and touching all over each other, thankful for our mutual emotions. I couldn’t believe that she felt the same, it almost felt dangerous thinking about it, as if that would take it away. But it was real, and she was there kissing me after saying yes to marrying me.

             “You know,” she purred after a while. “I was never one for the idea of ‘waiting till marriage’”

             “Well,” I slurred back. “I suppose we better get to it, because I’m not waiting too long to finalize this.”

             I picked her up, causing her to cackle, her head falling back. I stepped onto the elevator and clicked 6, going on to live the rest of our lives on our terms, together.

**Author's Note:**

> Also at: http://deansleather.tumblr.com/post/146751246008/auto-pilot


End file.
